Free Sex Advice
"My big dicked man is a big dick," sex advice from Dr. Dick
Name: Jack
Gender:
Age: 52
Location: Milwaukee
I’ve been dating this guy for over a year. He is the love of my life. I
love him so much, but he treats me like shit. I met him on vacation in
Florida. He’s 26 a stunning, 6’3” 200lbs, blond surfer Adonis. And
excuse me for being so graphic; he has the biggest dick I’d ever seen.
The first time we had sex I saw stars. He filled me up like no other
person has.
When I got home we exchanged emails nearly every day and even had some
hot phone sex a couple of times. He was down on his luck, because he
lost his barista job for coming to work stoned too many times. I know I
shouldn’t have, but I invited him to come live with me. I flew him up,
but I told him that this wouldn’t be a free ride, he’d have to stop
smoking so much dope and get a job and he agreed.
The sex was fantastic for the first couple of months, but once he
established himself as a star at the gym he found his own friends and
now I don’t see too much of him. He eats my food and drinks my liquor
and drives my car. I pay for his clothes and gym membership. He has yet
to find a job.
I know I should just end it, but I love him and I would really miss the
sex. My friends ridicule me for thinking he loves me as much as I love
him. They tell me they know he sees other guys. I’m so turned around I
don’t know what to do.
Like my momma always used to say: if it’s got wheels or a dick, you
know you’re gonna have problems with it. And I would add, if it’s got
big wheels or a big dick you know you’re gonna have BIG problems with
it.
Before we turn our attention to your no good boyfriend, let me make a few quick 
observations
about you. You’re a freakin’ mess, girlfriend! I mean really, you’ve
broken all the cardinal rules about dating a hustler. I know, I can
hear you now…oh no dr dick, he’s not a hustler; he’s a good kid who’s
just down on his luck and I’m just trying to help. Bullshit!
Ya see, that’s the first cardinal rule of dating a hustler is never
lose sight of the fact that he’s a hustler and you’re his john. Don’t
get me wrong; I have the deepest admiration for hustlers and their
johns. It’s just that this arrangement only works if everyone is clear
about the ground rules. And here are the ground rules — rich older
gentleman connects with needy younger hunky stud for mutual benefit.
Rich older gentleman keeps needy younger hunky stud in room and board,
booze, clothes, car, gym membership and the like; and needy younger hunky
stud buggers rich older gentleman senseless with his big blond
surfer-boy dick. Get it? Got it? Good!
Second cardinal rule — what happens on vacation should stay on
vacation. Vacation sex, as wonderful and delicious as it may be, does
not transplant very well to your non-vacation life. You’re more likely
to have success transplanting a delicate tropical orchid to your
Milwaukee backyard than transplanting a vacation hustler fuck to your
work-a-day world back home.
Third cardinal rule —don’t try to gloss a perfectly fine, fully
functional and even an affectionate hustler/john relationship with talk
of love. It’s unnecessary, unseemly and untrue. It’s lust, it’s
limerence, it’s love sickness, whatever…it’s just not love. Because
LOVE don’t ever make you feel as bad as you’re feelin’. Probably your
friends would have less difficulty with your mooning over this guy if
you were more honest about the nature of this relationship. They
wouldn’t be rubbing your face in the evidence that surfer-boy is
pluggin’ other dudes.
Fourth cardinal rule — a size queen, like you Jack, should admit that
you are enamored with the guy hose and how it fills you up plain and
simple. To pretend that you would string yourself out like this for a
guy with tiny meat is just that — pretense. Listen, there’s nothin’
wrong with bein’ a size queen, it’s the dishonesty I object to.
How is this young fella ever supposed to respect you when you don’t
respect for yourself? He probably had you pegged (no pun intended) back
on the beach in the sunshine state. He knows you will tolerate his
misbehavior, which of course gives him permission to do whatever he
feels like doing whenever he feel like doing it. And now he don’t even
have to give up the occasional mercy fuck any more, even though that was
surely part of the deal at the get go, right?
So the waif has yet to find a job after a year, huh? Why is that not
surprising? But even a hustler needs his mad money, besides what is
doled out to him by his long-suffering john. I’d be willing to guess
Mr. surfer dude is turning tricks to keep himself in weed and other
essentials.
Thing
is, this fellow probably would have treated you better if you would
have just stuck to the hustler/john script. Ya see, kids like this need
structure. He may have looked to you for this at one time, but when he
realized that he had you cock-whipped, the teachable moment
evaporated. This lad is probably like most other boys with big dicks.
They learn early on that their cock gives them enormous power, because
it is the object of desire for so many. He soon discovered that you
were no different than all the other men (and some women) in his life —
only interested in owning a piece of his sizeable endowment. And so he
turned the tables on you. You can hardly fault the guy. You try to
manipulate him with your money. He outwits you and manipulates you with
his dick.
If you’re really serious about reining in the little monkey, you’d
better come up with a clear, unambiguous message about what you will and
will not tolerate. And it better be something more than “I expect you
to bone my scrawny middle-aged ass on occasion.” Because, until you do,
he will roam wherever and whenever he wants.
There are many root causes for his behavior, just like there are many
root causes for your behavior. But since I’m talking to you, not him, I
suggest that you get to the bottom of all of this by investing a good
deal of time and energy with a competent sex-positive therapist. There’s
one thing I can say for certain, if the status quo continues your
resentment will boil over one day and there will be violence, the kind
of violence that you may not think yourself capable of now. But
violence there will be; you can bank on it!
Is there enough goodwill between the two of you to resolve this
unfortunate situation amicably? Who knows! If I had to guess, I’d say
there was a slim to no chance for that. If that’s the case, I advise
you pack him up and put him on the next plane south. And no more
relationships for you, particularly with unemployed young men with
massive schlongs, till you get your head screwed on tighter.
Good Luck Ya’ll
Dr. Dick
Originally published August 2010